NaNCO → n-[4-(3-Amino-1,2-benzisoxazol-4-yl)phenyl]urea

HRID 1593753Notes

Reaction equation

HRID 1593753 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]3[C:14]([NH2:17])=[N:15][O:16][C:12]=3[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[N-:18]=[C:19]=[O:20].[Na+]>CC(O)=O.O>[NH2:17][C:14]1[C:13]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:19]([NH2:18])=[O:20])=[CH:7][CH:6]=3)=[CH:9][CH:10]=[CH:11][C:12]=2[O:16][N:15]=1

Participants

5

Reactant 2

HCID 11051568NaNCOHCID 247683944-(4-Aminophenyl)-1,2-benzoxazol-3-amine

Product 1

HCID 11265647n-[4-(3-Amino-1,2-benzisoxazol-4-yl)phenyl]ureaYield 65.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of Example 261A (45 mg, 0.2 mmol) and sodium isocyanate (26 mg, 0.4 mmol) in HOAc (0.5 mL) and H2O (0.5 mL) was stirred overnight at rt, then diluted with water. The precipitated solid was collected by filtration and recrystallized from THF/hexanes to give an offwhite solid (35 mg, 65%). 1H NMR (300 MHz, DMSO-D6) δ ppm 5.20 (s, 2 H) 5.92 (s, 2 H) 7.11 (dd, J=7.3, 0.9 Hz, 1 H) 7.37 (d, J=8.5 Hz, 2 H) 7.46 (dd, J=8.5, 1.0 Hz, 1 H) 7.57 (d, J=8.5 Hz, 2 H) 7.57 (dd, J=8.1, 7.1 Hz, 1 H) 8.72 (s, 1 H) MS (ESI(+)) m/e 269.0 (M+H)30 .

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. customrecrystallized from THF/hexanes

Sources & evidence

ORD record
ord-a9a1ec5995464e32bdb095e975908acf
Source dataset
uspto-grants-2007_11
Patent number
US07297709B2

Reaction notes

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